Ascorbate 2-polyphosphate esters and method of making same

Details Ascorbate 2-polyphosphate esters and method of making same Ascorbate 2-polyphosphate esters and method of making same

1985-06-25

1987-03-03

Raymond, Richard L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07F 909

Patent

active

046476725

ABSTRACT:
A new stable derivative of ascorbic acid, ascorbate 2-polyphosphate, is disclosed, together with a high-yield method of synthesis thereof. The method preferably includes steps of reacting an ascorbic acid such as L-ascorbic acid or a derivative thereof such as 5,6-O-isopropylidene-L-ascorbic acid with salts of metaphosphoric acid in an aqueous system and in the presence of sufficient base to maintain the pH of the reaction mixture at a level of at least above 9 to obtain 2-polyphosphorylation of the ascorbic acid. In particularly preferred forms, 1 M L-ascorbic acid is reacted in water with 1.5-3 equivalent of sodium or potassium trimetaphosphate at a temperature of 25.degree.-55.degree. C., and an alkali metal hydroxide such as potassium hydroxide is intermittently added to the reaction mixture as needed over a 1-10 hr. reaction period to maintain the pH thereof at a level of about 10.5-12 during the entire reaction. After neutralization the reaction mixture contains no noxious or toxic materials, and the entire mixture may be added to food or feed. Pure salts of ascorbate 2-triphosphate can be isolated readily using conventional chromatographic techniques. It has also been found that the compounds of the invention are more difficult to oxidize, and release ascorbic acid and are more slowly hydrolyzed than the monophosphate derivative of ascorbic acid.

REFERENCES:
patent: 4179445 (1979-12-01), Seib et al.
Nomura et al, Chemical Abstracts, vol. 74 (1971), 31939v.

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